To no one's surprise, Microsoft has probably one of the worst user experiences.
Trying to send an email. Takes forever and returns an error that says something like "There was an error, please click here for more details." And the more detail returns: "This message can't be sent right now. Please try again later."
Great, Microsoft, great.
I eventually figured it out. The issue was that I was tagging a private group. It was a group set up in my outlook with a bunch of people that I send to normally. This is separate from Active Directory because I don't have access and I hate dealing with admin support.
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